Synthesis of alpha- and beta-glycosides containing spin labels, as probes for studies of carbohydrate-protein interaction.
Nitroxide spin-labeled alpha-D-glycopyranosides were synthesized in good yield and in a highly stereoselective manner by reaction of per-O-benzyl-alpha-D-glycopyranosyl bromides with 2,2,6,6-tetramethyl-4-piperidinol under the bromide ion-catalyzed conditions devised by Lemieux et al. After hydrogenolysis, the deblocked intermediates were oxidized to give the desired, spin-labeled alpha-D-glycopyranosides. Nitroxide spin-labeled beta-D-glycopyranosides, as well as a beta-maltoside, were synthesized by standard methods. The synthesis is also described of 2-amino-2-deoxy-D-glucose and -D-galactose derivatives having a spin label at C-2, and of the spin-labeled compound 1-[4-(beta-D-galactopyranosyloxy)phenyl]-3-(2,2,6,6-tetramethylpiperidin-1-oxyl -4-yl)-2-thiourea.
D000818:Animals; D002417:Cattle; D004926:Escherichia coli; D005697:Galactosides / Q000138:chemical synthesis*; D006023:Glycoproteins; D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008297:Male; D013113:Spin Labels / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship; D013737:Testis / Q000201:enzymology; D001616:beta-Galactosidase
D005697:Galactosides; D006023:Glycoproteins; D006027:Glycosides; D007202:Indicators and Reagents; D013113:Spin Labels; D001616:beta-Galactosidase